To be clear, I have nothing against going enlisted in the military. I work with a lot of very talented and motivated enlisted airmen/NCOs who are damn good at what they do and many of them seem quite satisfied with their career choice. However if the goal is to be a pilot, that path in the USAF doesn't go through the enlisted ranks. Pilots who are prior enlisted face significant additional challenges both before they even get to pilot training, and with career management afterwards due to their age and time in service.
As for enlisting in the Navy, Army, Marines... If that's what you want to do then by all means go for it. The military is in turmoil right now due to constant shifting and thrashing from senior leadership from "hey we have too many lets kick some out", full swing to "hey we don't have enough, lets do what we can to not let people leave", with really bizarre policies constantly oming down the pipe. Like one year they brought back a whole bunch of retired Lt Cols pilots to go back into flying jobs, and the very next year they involuntarily separated (with ZERO retirement!) a bunch of 14-15 year majors. Utter incompetence and indecision rules the personnel office today. So yea, turmoil in the services is a mild way of saying it.
HOWEVER, there are some things in life that you can only do in the military. If the thing you want to do can only be done in the military, then please join up. We need people in the ranks who are motivated about serving and dedicated to staying in and doing it right. In spite of all the weirdness going on now, I've had a great 25 years wearing the uniform and I'm not done yet. I've done and seen things that most people can only dream of, travelled around the world, etc etc. Most people have to pay money to do the things that I get paid for. Few careers offer that kind of opportunity. So yea, if you really want to be in the military, go for it. Just do it with your eyes open and have a clearly defined path from where you are to where you want to be. Don't deviate from that path or you'll probably never get back on it. If you want to be a pilot, you need a degree, a commission, a medical clearance, selection for UPT, graduation from UPT, and graduation from initial mission qualification training in a formal training unit. Some of those steps are competitive so you have to be better than the others who are trying to do the same thing. And you can be bumped out of line at any of those steps by a number of issues, whether they're self-induced (like getting a DUI or something dumb), or totally out of your control like getting a brain tumor or something.
If you can make it through though, there's no other job like it. And that's true for any of the selective specialties in each of the services. Find the path to get what you want, and stay on that path no matter what.
Finally, even though you've done some college, don't discount the service academies. It doesn't hurt to inquire about the application process and older cadets with some college experience are often at a slight advantage over younger cadets coming straight out of high school. If you do apply for the academy however, take the time to submit a good enthusiastic application package and approach the interviews (liaison officer and congressional rep at a minimum) with great enthusiasm. If you don't seem dedicated to going to the academy, they'll pick someone who is.
The USAF academy sends the most 2Lts to pilot training out of all the commissioning sources. In some years, 100% of medically qualified academy grads are offered a pilot training slot. Even in the bad years, more academy grads go (as a percentage of the eligible officers) than any other source. That's the best chance of getting selected, and that's why I fought to get into the USAF academy. Took me 2 years to get in but it was worth it.
